Seven new tanzawaic acid derivatives, steckwaic acids E-K (-), and one new benzene derivate (), together with seven known tanzawaic acid analogues (-) were isolated from the marine algicolous fungus SCSIO 41040. The structures and absolute configurations of these new compounds (-) were determined by spectroscopic analyses, X-ray diffraction, and comparison of ECD spectra to calculations. Compounds , , and inhibited lipopolysaccharide (LPS)-induced nuclear factor kappa-B (NF-κB) with IC values of 10.4, 18.6, and 15.2 μM, respectively. Compound could suppress the receptor activator of NF-κB ligand (RANKL)-induced osteoclast differentiation in bone marrow macrophage cells (BMMCs). To the best of our knowledge, this is the first report of osteoclastogenesis inhibitory activity for tanzawaic acid derivatives.
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http://dx.doi.org/10.1021/acs.jnatprod.2c00865 | DOI Listing |
J Med Chem
February 2024
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
To discover novel osteoclast-targeting antiosteoporosis leads from natural products, we identified 40 tanzawaic acid derivatives, including 22 new ones (-, -, -, , and ), from the South China Sea mangrove-derived fungus SCSIO 41025. Penicisteck acid F (), one of the new derivatives showing the most potent NF-κB inhibitory activity, remarkably inhibited osteoclast generation . Mechanistically, reduced RANKL-induced IκBα degradation, NF-κB p65 nuclear translocation, the activation and nuclear translocation of NFATc1, and the relevant mRNA expression.
View Article and Find Full Text PDFACS Omega
August 2023
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
The first total synthesis of (+)-tanzawaic acid B, a natural polyketide bearing a pentadienoic ester and octalin moiety, has been accomplished. The synthetic improvement from previous synthetic conditions facilitated our gram-scale synthesis of the chiral octalin that possesses seven stereogenic centers and that is the core skeleton of almost all of the tanzawaic acid family.
View Article and Find Full Text PDFJ Nat Prod
May 2023
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, People's Republic of China.
Seven new tanzawaic acid derivatives, steckwaic acids E-K (-), and one new benzene derivate (), together with seven known tanzawaic acid analogues (-) were isolated from the marine algicolous fungus SCSIO 41040. The structures and absolute configurations of these new compounds (-) were determined by spectroscopic analyses, X-ray diffraction, and comparison of ECD spectra to calculations. Compounds , , and inhibited lipopolysaccharide (LPS)-induced nuclear factor kappa-B (NF-κB) with IC values of 10.
View Article and Find Full Text PDFFitoterapia
January 2023
College of Life and Health, Dalian University, Dalian 116622, China.
Seven undescribed polyketide compounds (1-4, 9-11) and six known polyketide compounds (5-8,12, 13) were isolated from Rhodiola tibetica endophytic Penicillium sp. HJT-A-10. The structural of seven undescribed polyketides metabolites were established on the basis of spectroscopic methods.
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